Pyrazolone dyes and process of making them.



U NITED STATESPATENT OFFICE.

PAUL JULIUS AND ERNST FUSBENIEGGER, OF LUDWIGSHAFEN-ON-THE-RHINE, GER- MANY, ASSIGNORS TO BADISCHE ANIL'IN 8c SODA FABHIK, OF LUDWIGSHAFEN-ON- THE-RHINE, GERMANYJA CORPORATION.

PYRA'ZOLONE DYES'AND PROCESS OF MAKING THEM.

No Drawing.

in which either R, or R or both, represent the 2-nu-tligrl-6-bro1n-benzeue-4-sulfonic acid reeidue. The coloring matters of the formula in which R and R both represent the szlitl residue can he obtained, for instance, by l wauhining dihydroxytartaric acid with two molecular proportions of the hydruzin of iihroiu-Q -aminol onethyl-henzenw fi-sulfonig acid. It is preferrodto produce thosein which R and R, diti'er'from one'anothcr by acting with a hydrazin on oxalyl aeetic'ester and then upon the compound containing the pyruzoloue ring formed withadiazo compound.

For the urposes: of ourinrention, either the hydramn or the di'azo,'cou|pound', of both, must he drri-red from the 8 hronr-2 amino -l' methyi ibeniene fiy snlfonic acid. The coloringmatters soobtained-yield pan aha) vei'y-fastmguinst the action of liglm The oolorm "matters containing the 2- methyl-ti-bromenzenet-sulfonie acid group Specification of Letter; Patent.

Application flied November 4, 1919. Serial No. 590.695.

Patented Dec. 5. 191 1.

twice possess exceptionally greenish shadesof vellow when in the form of lakes.

)ur new coloring matters consist. when dry, of yellow powders. they are soluble in water yielding from yellow to green-yellow solutione, they (lye wool yellow and in the form of their-lakes 105K055 a. yellow color and are fast to light nm N )Hl] reduction with tin and hydrochloric lll'll the? yield a pyrazw lone of a constitution corresponding to the formula nooe-e :=x-xn-co-clmm and an main of a constitution corresponding to the formula R NH either R or R or both R and R being 2-methyl-6-brom-benzene-i-sulfoniu acid. The shades which they produce on wool are generally less greenish yellow than those obtained from the corresponding ehlorin compound. The coloring matter which we desire to be understood as claiming specifically is that in which both R and R represent the 2-meth l-G-hrmnbenzene-4-sulfonic acid residue. t yields a greenislryellow solution in water. i

The following examples will serve to illustrate further the nature of our invention and how it can he carried into practical eil'eet, but the invention is not confined to these examples. The parts are by weight.

ExmnYle iztitir eleven parts of the sodium sa t of dihydro -tartaric acid with fifty parts of water, an add a suspension of twenty eight and one-tenth parts of the hydrazin of 3-lmau-Q-amino-I methyl'benzene- '5-sulfonic 'iu'id'iu liftyparta'of water. (in

lirating'th'e mixtu'in'm fir-:1. in about. iii'ly degreesfientigiade"and then, gradually. .to v "Pooh i'('2ll l (l'thlt'. (ilut|on"talces' place gem-halite 'lla roloc mg mattercan lie isolated in prwipitatioa with common Salt, or with potassium rhlorid, if des1red,'after having acidified the solution. Filter oil the coloring matter, and press and dry it. Itgives rise to lakes which possess very pure lemomyellow shades of excooa. C I

a 1 N H-N H1 t somiv Example 2: Diazohze twenty-six and three-fifths parts of 3-brom-2-amino-1 methy'l-benzene-fi-sulfonie acid in the usual manner and allow the solution to run while stirring," into a concentrated solution of thirty parts of l-parwsulfo-phen I-5- yrazolone-3-carboxylie acid, to wide: su cient sodium carbonate has been added to mainta'i'in the whole alkaline. Stir for about half som.

CF) N=N- Now what we claim is z--- 1. The process of producing colorin matters of the pyrazolone group by eom ining dihydroxy-tartaric acid with two molecular proportions of the hydrazin of 3-ln'om-2- amino-l-methyl-benzene-5-snltonic acid.

2. The new coloring matters of the pyrazolone group which consist when dry of yellow powders, are soluble in water yieldmg from yellow to green-yellow solutions,

dye wool yellow and in the form of their lakes possess a yellow color and are fast to light and upon reduction with no .and hydrocllloric acid yield a pyrazolmle f a con-- stitution corresponding to the formula:-

no0o-c-u-ua-co-cu.mn

and an amin of a constitution corresponding to the formula. R NIlone at least of the roups R and R being 2-methyl-6-bromenzene--sulfonic acid.

3. The new coloring matter of the pyrazcellent fustness against the action of light.

The reaction which takes place may be rep:

resented by the equation soma CHI - an.o.

an hour, then heat to fifty degrees centigrade and precipitate the coloring matter by means of common salt, if desired after first having ncidified the solution. Filter off the colormg matter and press and dry it. It yields a yellow solution In water and dyes wool pure yellow shades. The reaction which takes place may be represented by the equation and an nmin of a, constitution eorrespomliug to the formula ll Nll both of the groups R, and ll being 2-nlethyl-fi-brom-l enzenc-4- sulfonic acid.

In testimony whereof we have hereunto set our hands in the presence of two subscribing witnesses.

PAUL JULIUS. ERNST FUSS ENEGGER. Witnesses: Enuns'r F. Enmmno'r, A. O. -'lr'rr.\n\xu. 

